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I love great conversations about technology – especially ones where the answer is not very neatly settled into winners and losers (which is ALL of them in IT). I’m excited that RackN has (re)launched the L8ist Sh9y (aka Latest Shiny) podcast around this exact theme.

Please check out the deep and thoughtful discussion I just had with Mark Thiele (notes) of Aperca where we covered Mark’s thought on why public cloud will be under 20% of IT and culture issues head on.

In this 7th Installation IN AN 8 POST SERIES, BRAD SZOLLOSE AND ROB HIRSCHFELD INVITE YOU TO SHARE IN OUR DISCUSSION ABOUT FAILURES, FIGHTS AND FRIGHTENING TRANSFORMATIONS GOING ON AROUND US AS DIGITAL WORK CHANGES WORKPLACE DELIVERABLES, PLANNING AND CULTURE.

The Duality Trap is one digital management danger that’s so destructive, we felt this series would be incomplete without a discussion. It’s especially problematic for The Digital Native managers and often mishandled by traditionally trained ones too.

Each apple is delicious. Which would you choose?

The Duality Trap occurs when there are multiple right answers to a question. How often does this happen? Every single time. In fact, it’s a side effect of good digital management. Why?

In hierarchical management, the boss is always right so there’s no duality. Since we’ve thrown out hierarchical decision making, every team action is potentially subject to review by everyone on the team. The very loose structure that allows individual autonomy and rapid response has the natural consequence of also creating cognitive friction when individuals approach problems differently.

These different approaches are generally all valid ways to progress.

Digital natives fundamentally understand choice duality and may present alternatives just to ensure team diversity. Unfortunately, while where may be multiple valid solutions, the team can only pick one [1]. Nine times out of ten, the team will simply pick and move on. In that outlier case, they are counting on you, their digital manager, to resolve the selection.

Here’s the trap: resolving a duality does not mean “picking the winner” because having a winner implies the choices were unequal. If you’re team is stuck then there are at least two good choices.

If you are a traditional manager, the temptation to become Ronald “the decider” Reagan is nearly irresistible. Under the title=authority to decide model, you must justify your salary with making a “right” decision. You’ve been waiting for this moment to exert your authority for days. But, unbeknownst to “the decider,” this big moment will immediately undermine the team’s autonomy. On the other hand, If you are a digital native then this is the moment you’ve been dreading because you’ve got to be decisive. Despite 5 to 10 really good choices, you have to make ONE. So, a digital native can appear to be indecisive. However, not deciding is the worst possible choice. So what should you do?

First, remember that teams are strengthened when they are clearly aligned around an intent.

Resolving the duality trap is an opportunity to emphasize your intent. The best approach is to ask your team to review the options again in light of your shared objectives. In many cases, they will be able to resolve the issue from that perspective. If not, then you should:

validate all options could work

have the team state desired outcomes that can be measured

pick the option that most aligns with your intent

ask if the option your team does choose fit the overall agenda of; speed of delivery but quality drops, quality of deep diving into the project (upping the quality) but you may miss a crucial deadline (this may narrow down your choices.

ask the team to monitor for the results

In this case, even as you are driving a decision, you are still sharing the responsibility for the outcome with the team. It’s important for the team that you focus on the desired results and not on which course was chosen. It is very likely that any of the choices would work out and achieve positive outcomes.

So it’s OK to get out of the trap of picking “best” options when there are multiple right choices.

In an age of ambiguity, it is easy to fall into the duality trap. Just remember, there is no one way to get it all done these days. Which means a GREAT people manager realizes 2 things; a) your people need more of your support than ever. This comes in the form of training, finding solutions, and building a team that has the right chemistry. And b) getting out of their way.

In this 6th Installation IN AN 8 POST SERIES, BRAD SZOLLOSE AND ROB HIRSCHFELD INVITE YOU TO SHARE IN OUR DISCUSSION ABOUT FAILURES, FIGHTS AND FRIGHTENING TRANSFORMATIONS GOING ON AROUND US AS DIGITAL WORK CHANGES WORKPLACE DELIVERABLES, PLANNING AND CULTURE.

Our advice comes down to very simple concept: Today’s leaders MUST walk the talk.

Management authority in digital work comes from being the owner of the intention. Your team is working towards a shared goal. That is their motivation and it’s required for digital managers to provide a clear goal – this is what we call the intent of your organization. So a manager’s job comes down to sharing your organization’s intent.

Like the 80’s “management by walking around,” walking the intent means that you spend most of your time helping your team understand the goals, not telling them how to achieve greatness. Managers provide alignment, not direction.

What does digital management look like:

Pick a tone and repeat, repeat, repeat – You are the Jazz leader setting the tempo and harmony, your consistency allows others to improvise. If you set the stage, you can encourage others to take the lead off your base. Strong management is not about control. Strong management is about support. Support that streamlines productivity.

Encourage cross-communication – Better, make people talk to each other. it’s OK to proxy, but don’t carry opinions for your reports as if they were your own. And don’t be upset if someone goes “above” you in the hierarchy. There is no such thing anymore.

1-to-1 communication is healthy – do a lot of it. 1) Don’t make decisions that way. 2) Don’t get stuck having 1-to-1 with the same people. 3) a lot of informal/small interactions are OK. Diversity is key. You may have to reply/rehash/proxy a whole 1-to-1 discussion for your team

Learn your Culture – This may be the hardest thing for leaders to do because if they always assumed that culture didn’t matter. In today’s work environments, culture matters more than you could imagine. Just ask Peter Drucker! Knowing who does what is important. Knowing how each individual communicates and what their strengths and weaknesses are is even more important.

“Yes, AND…” The cornerstone of Improv is about saying yes to ideas, even fragile ones. Then it becomes about testing, experimenting and pushing boundaries. This is where innovation comes from. Saying yes and, instead of no but, ensures things get customized. Yes, you might fail, but fail fast, and move on.

Be forceful on time keeping – make sure debates and discussions have known upfront limitations. Movement is good, uncertainty is frustrating.

Check and adjust – check and don’t change is just as important. The key is to involve your team in the check-ups. When you decide not to adjust, that’s also a decision to communicate.

Don’t apologize for or delay making top down decisions – not all actions are team discussions. Sometimes, the team process is tiring and hard so the most strident voice wins. No team always agrees so don’t be afraid to play the role of arbitrator.

Fix personnel issues quickly – allowing people to abuse the system drives away the behaviors that you want. Focus instead on strengths, and become the mediator. Be very sensitive to stereotypes and even mild no name calling. Focus on the work, the outcomes and how everyone can do better. then hold them accountable to their word.

Ask people to define their own expected results – then keep them accountable. When they miss, have no-blame a post-mortem that focus on improvement. A term called the Feedback Sandwich helps by starting a difficult conversation with something a team member did right, then work your way through the conversation to the “meat” part of the sandwich: what they did that needed help, improvement or an admission that they might NOT be the person best qualified for that task. Let them state this on their own by asking better questions.

Assume failures are from system, not individual – work together to fix the system. Communication and hand off are usually the biggest fails when meeting deadlines. Find solutions from the team. after all, who knows development operations better than the people working in it.

Be careful about highlighting “grenade divers” [1] – All organizations need heroes, but feeding them will erode team performance. Once, they may have saved the day. When it becomes a habit, they might be creating the chaos they are always solving in order to have job security. After all, they seem to be the only one who can solve that problem…every time. In a symphony only a few get the solo. In Jazz, you play both solo and support. That flexibility gives your team strength.

These ideas may push your outside your comfort zone. Find a peer for support! You need to to be strong to lead from the back.

Even without formal hierarchies, manager roles are still needed to drive value and make the hard calls. Before, that translated into make all the decisions. The new challenge is to allow for free falls (post 4) while sharing the responsibility.

If you walk your intent and communicate goals consistently then your team will be able to follow your lead.

[1] Grenade Diving or “wearing the cape” is a team anti-pattern where certain individuals are compelled to take dramatic actions to rescue an adverse situation. While they often appear to be team heroes (Brad saved the batch of cookies again! Who forget to set the timer?), the result always distracts from the people who work hard to avoid emergencies. We want people to step up when required but it should not become a pattern.

Fifth IN AN 8 POST SERIES, BRAD SZOLLOSE AND ROB HIRSCHFELD INVITE YOU TO SHARE IN OUR DISCUSSION ABOUT FAILURES, FIGHTS AND FRIGHTENING TRANSFORMATIONS GOING ON AROUND US AS DIGITAL WORK CHANGES WORKPLACE DELIVERABLES, PLANNING AND CULTURE.

Digital Management has a challenging deep paradox: digital workers resist direct management but require that their efforts fit into a larger picture.

If you believe the next generation companies we discussed in post #4, then the only way to unlock worker potential is enable self-motivated employees and remove all management. In Zappos case, they encouraged14% of their workers to simply leave the company because they don’t believe in extreme self-management.

Companies like W. L. Gore & Associates, the makers of GORE-TEX, operate and thrive very well in a team-driven environment… This apparently loosey-goosey management style has brought about hundreds of major multibillion-dollar ideas and made W. L. Gore a leading incubator of consistently great ideas and products for more than fifty years. To an outside observer it looks as though the focus is on having fun. But to the initiated, it is about hiring intense self-starters who contribute wholeheartedly to what they are doing and to the team, and most important, who can self-manage their time and skill sets.

— Liquid Leadership by Brad Szollose, page 154

Frankly, both of us—Brad and Rob—are skeptical. We believe that these tactics do enhance productivity, but gloss over the essential ingredient in their success: a shared set of goals.

Like our Jazz analogy, the performance is the sum of the parts and the players need to understand how their work fits into the bigger picture. A traditional management structure, with controlling leadership and über clear, micromanaged direction, backfires because it restricts the workers’ ability to interpret and adapt; however, that does not mean we are advocates of “no management whatsoever” zones.

The trendy word is Holacracy. That loosely translates into removal of management hierarchy and power while redistributing it throughout the organization. Are you scared of that free-fall model? If workers reject traditional management then what are the alternatives?

We need a way to manage today’s independent thinking workforce.

According to Forbes, digital workers have an even higher need to understand the purpose of their work than previous generations. If you are a Baby Boomer (Conductor of a Symphony), then this last statement may cause you to roll your eyes in disagreement.

Directing a Jazz ensemble requires a different type of leadership. One that hierarchy junkies —orchestra members who need a conductor—would call ambiguous…IF they didn’t truly know what was happening.

Great musicians don’t join mediocre bands; they purposely seek out other teams that are challenging them, a shared set of goals and standards that produce results and success. This may require a shift in mindset for some of our readers.

Freedom in jazz improvisation comes from understanding structure. When people listen to jazz, they often believe that the soloist is “doing whatever they want.” If fact, as experienced improvisers will tell you, the soloist is rarely “doing whatever they want”. An improvisational soloist is always following a complicated set of rules and being creative within the context of those rules. From Jazzpath.com

In the past generation, there was no need to communicate a shared vision: you either did what you were told, OR just told people what to do. And people obeyed. Mostly out of fear of losing your job. But, in the digital workforce, shared goals are what makes the work fit together. Players participate of their own will. Not fear.

Putting this into generational terms: if you were born after 1977 (aka Gen X to the Millennials) then you were encouraged to see ALL adults as peers. In the public school system, this trend continued as the generation was encouraged to speak up, speak out and make as many mistakes as possible…after all, THAT is how you learn. And the fear of screwing up and making mistakes was actually encouraged, as teachers also became friends and mentors. Video games simply reinforced the same iterative learning lessons at home.

Thousands of years of social programming were flipped over in favor of iterative learning and flattened hierarchy. Those skills showed up just in time to enable us to survive the chaos of the digital work / social media revolution.

But survival is not enough, we are looking for a way to lead and win.

Since hierarchy is flat, it’s become critical to replace directing action with building a common mission. In individual-centric digital work, there are often multiple right ways to accomplish the team objective (our topic for post 7). While having a clear shared goals will not help pick the right option, it will help the team accept that 1) the team has to choose and 2) the team is still on track even if some some individuals have to change direction.

Just listen to the most complex work out there that has been influenced by Jazz; the late Jeff Porcaro, pop rock drummer and cofounder of Toto admits to being influenced by Bo Diddley for his drum riffs on the song Rosanna. Or if you are a RUSH fan you know that songs like La Villa Strangiato owe the syncopated rhythms, chord changes and drum riffs to Jazz.

Or the modern artist Piet Mondrian who invented neoplasticism, was inspired by listening incessantly to a particular type of jazz called “Boogie-Woogie.”

Participants in this type of performance do not tune out and wait for direction. They must be present, bring 100% of themselves to each performance, and let go of what they did in the last concert because each new performance is customized.

You have until our next post to cry in your beer while whining that digital managers have it too hard. In the next post, we’ll lay out 12 very concrete actions that you should be taking as a leader in the digital workforce.

PS: Brad some important insights about how their childhood experience shapes digital natives’ behavior. We felt that topic was important but external to the primary narrative so Rob included them here:

Third IN AN 8 POST SERIES, BRAD SZOLLOSE AND ROB HIRSCHFELD INVITE YOU TO SHARE IN OUR DISCUSSION ABOUT FAILURES, FIGHTS AND FRIGHTENING TRANSFORMATIONS GOING ON AROUND US AS DIGITAL WORK CHANGES WORKPLACE DELIVERABLES, PLANNING AND CULTURE.

First, has work really changed? Yes. Traditionally there was a distinct difference between organized production and service-based/creative work such as advertising, accounting or medicine. Solve a problem by looking for clues and coming up with creative solutions to solve it.

Digital work on the other hand, and more importantly – digital workers, live in a strange limbo of doing creative work but needing business structures and management models that were developed during the industrial age.

In today’s multi-generational workforce, what appears to be a generational divide has transformed into a non-age-specific cultural rift. As Brad and Rob compared notes, we came to believe that what is really happening is a learned difference in the approach to work and work culture.

There is learned difference in the approach to work and work culture that’s more obvious in, but not limited to, digital natives.

In most companies, the executives are traditionalists (Baby Boomers or hand-selected by Boomers). While previous generations have been trained to follow hierarchy, the new culture values performance, flexibility and teamwork with a less top-down control oriented outlook.

It’s like a symphonic conductor who is used to picking the chair order and directing the tempo is handing out sheet music to a Jazz ensemble. So how is the traditional manager going to deliver a stellar performance when his performers are Jazz trained?

In traditional concert orchestra, each musician has to go to college, train hard, earn a shot to get into the orchestra, and overtime, work very hard to earn the First Chair position (think earning the corner office). Once in that position, they stay there until death or retirement. Anyone who deviates, is fired. Improv is only allowed during certain songs, by a select few. It’s the workplace equivalent to climbing the corporate ladder.

Most digital workers think they belong to a Jazz ensemble.

It’s a mistake to believe less organized means less skilled. Workers in the Jazz model are also talented and trained professionals. If you look at the careers of Thelonius Monk, Duke Ellington and Dizzy Gillespie, they all had formal training, many started as children. The same is true for digital workers: many started build job skills as children and then honed their teamwork playing video games.

But can a loosely organized group consistently deliver results? Yes. In fact, they deliver better results!

When a Jazz Improv group plays, they have a rough composition to start with. Each member is given time for a solo. To the uninitiated there appears to be no leaders in this milieu of talent, but the leader is there. They just refuse to control the performance; instead, they trust that each member will bring their A Game and perform at 100% of their capacity.

In business, this is scary. Don’t we need someone to check each person’s work? People are just messing around right? I mean, is this actual work? Who is in charge?

In business￼s environments that operate more like Jazz, studies have proven that there is a 32% increase in productivity from traditional command and control environments driven by hierarchy.

Age, experience and position are NOT the criteria for the Digital Worker. Output is. And output is different for each product. Management’s role in this model is to get out of the way and let the musicians create. Instead of conforming to a single style and method, the people producing in the model each bring something unique and also experience a high degree of ownership.

This is a powerful type of workplace diversity: by allowing different ways of problem solving to co-exist, we also make the workplace more inclusive and collaborative.

Sound too good to be true? In our next post we’ll discuss trust as the critical ingredient for Jazz performance. (Teaser)

In this 8 post series, Brad Szollose and Rob hirschfeld invite you to share in our discussion about failures, fights and frightening transformations going on around us as digital work changes workplace deliverables, planning and culture.

Digital workers will not deliver. Not if you force them into the 20th century management model then they (and you) will fail miserably; however, we believe they can outperform previous generations if guided correctly. In the 21st Century, digital technologies have fundamentally transformed both the way we work and, more importantly, how we have learned to work.

So far, we’ve framed this transformation as a generational (Boomers vs Millennials) challenge; however, workers today transcend those boundaries. We believe that we need to redefine the debate from cultural viewpoints of Boomers (authority driven leadership) and Millennials (action driven leadership). In the global, digital workforce, these perspectives transcend age.

We looked to performing music as a functional analogy for leadership.

In music, we saw very different leadership cultures at work in symphonic and jazz performances. The symphony orchestra mirrors the Boomer culture expectation of clear leadership hierarchy and top-down directed effort. The jazz band typifies the Millennial cultural norms of fluid leadership based on technical competence where the direction is a general theme and the players evolve the details. Both require technical acumen and have very clear rules for interaction with the art form. More importantly, these two extremes both produce wonderful music, but they are miles apart in execution.

Today’s workforce generations often appear the same way – unable to execute together. We believe strongly that, like symphonies and jazz concerts, both approaches have strengths and weaknesses. The challenge is to understand adapt your leadership cultural language of your performers.

That is what Brad and Rob have been discussing together for years and, now, we’d like to include you in our conversation about how Cloud Culture is transforming our work force.

PMs starting this group already direct the work for a super majority (>66%) of active contributors.

The primary mission for the group is to collaborate and communicate around development priorities so that we can ensure that project commitments get met.

It was recognized that the project technical leads are already strapped coordinating release and technical objectives. Further, the product managers are already but independently engaged in setting strategic direction, we cannot rely on existing OpenStack technical leadership to have the bandwidth.

This effort will succeed to the extent that we can help the broader community tied in and focus development effort back to dollars for the people paying for those developers. In my book, that’s what product managers are supposed to do. Hopefully, getting this group organized will help surface that discussion.

This is a big challenge considering that these product managers have to balance corporate, shared project and individual developers’ requirements. Overall, I think Allison Randall summarized our objectives best: “we’re herding cats in the same direction.”